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This limitation is particularly evident for spin-forbidden processes such as intersystem crossing (ISC), which are difficult to regulate through supramolecular design. The heavy-atom effect, although central to promoting ISC, is typically regarded as an intrinsic substituent property rather than a geometry-dependent supramolecular parameter. Here we show that macrocycle-directed supramolecular predisposition can deliberately enforce intramolecular heavy-atom effects to activate latent spin-forbidden transitions, enabling efficient self-sensitized oxidation. Encapsulation of a flexible aldehyde- and bromine-substituted guest within cucurbit[8]uril (CB[8]) enforces a folded geometry that juxtaposes the heavy atom and reactive aldehyde, as established by solution studies and single-crystal analysis. Under white-light irradiation, this predisposed complex undergoes selective oxidation of the aldehyde to the corresponding carboxylic acid. Control experiments varying heavy-atom identity, cavity size, and guest binding modes define CB[8]-enforced spatial juxtaposition as the critical structural requirement, while scavenger and EPR studies support triplet-oxygen energy transfer to generate singlet oxygen as the operative pathway. Preferential binding of CB[8] to the substrate over the product mitigates product inhibition and allows catalytic turnover under substoichiometric host loadings. These results show that macrocyclic encapsulation does more than statically stabilize a host\u2212guest complex: it transforms spatial geometry into a structurally gated switch for spin-forbidden pathways, establishing supramolecular predisposition as a versatile design principle for developing switchable photocatalysts and conformationally responsive smart materials.<\/jats:p>","DOI":"10.1021\/jacs.6c06445","type":"journal-article","created":{"date-parts":[[2026,7,15]],"date-time":"2026-07-15T20:02:55Z","timestamp":1784145775000},"page":"31054-31062","source":"Crossref","is-referenced-by-count":1,"title":["Supramolecular Predisposition\nPromotes Intramolecular\nHeavy-Atom Effects for Self-Sensitized Oxidation"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-5864-392X","authenticated-orcid":true,"given":"Fei","family":"Li","sequence":"first","affiliation":[{"name":"Jilin University , , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0450-5391","authenticated-orcid":true,"given":"Yibin","family":"Sun","sequence":"additional","affiliation":[{"name":"Jilin University , , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9690-5992","authenticated-orcid":true,"given":"Guanglu","family":"Wu","sequence":"additional","affiliation":[{"name":"Jilin University , , ,","place":["Changchun, P. R. China, 130012"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,15]]},"reference":[{"key":"2026073021262282200_cit1","doi-asserted-by":"publisher","first-page":"256","DOI":"10.1038\/s41565-020-0652-2","article-title":"Chemical Reactivity under Nanoconfinement","volume":"15","author":"Grommet","year":"2020","journal-title":"Nat. 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Soc."},{"key":"2026073021262282200_cit5","doi-asserted-by":"publisher","first-page":"1629","DOI":"10.1021\/acs.chemrev.4c00505","article-title":"Covalent Template-Directed Synthesis: A Powerful Tool\nfor the Construction of Complex Molecules","volume":"125","author":"Bolgar","year":"2025","journal-title":"Chem.\nRev."},{"key":"2026073021262282200_cit6","doi-asserted-by":"publisher","first-page":"879","DOI":"10.1039\/D3SC05343A","article-title":"Dynamic Covalent Synthesis","volume":"15","author":"Cougnon","year":"2024","journal-title":"Chem.\nSci."},{"key":"2026073021262282200_cit7","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211387","article-title":"The Story\nof the Little Blue Box:\nA Tribute to Siegfried Hu\u0308nig","volume":"62","author":"Chen","year":"2023","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026073021262282200_cit8","doi-asserted-by":"publisher","first-page":"263","DOI":"10.1017\/S1062798709000805","article-title":"Towards\nComplex Matter: Supramolecular Chemistry and Self-Organization","volume":"17","author":"Lehn","year":"2009","journal-title":"Eur. Rev."},{"key":"2026073021262282200_cit9","doi-asserted-by":"publisher","first-page":"13712","DOI":"10.1002\/anie.202000045","article-title":"Supramolecular Strategies\nfor Controlling Reactivity within Confined Nanospaces","volume":"59","author":"Wang","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026073021262282200_cit10","doi-asserted-by":"publisher","first-page":"11105","DOI":"10.1039\/D5CS00835B","article-title":"Supramolecular Catalysis with Emerging, Functional\nOrganic Macrocycles and Cages","volume":"54","author":"Ning","year":"2025","journal-title":"Chem. Soc. 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Chem.\nSoc."},{"key":"2026073021262282200_cit14","doi-asserted-by":"publisher","first-page":"15688","DOI":"10.1002\/anie.201706487","article-title":"Cucurbit[7]uril\nas a Supramolecular Artificial Enzyme for Diels\u2212Alder Reactions","volume":"56","author":"Palma","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026073021262282200_cit15","doi-asserted-by":"publisher","first-page":"11806","DOI":"10.1021\/jacs.9b05604","article-title":"A Supramolecular\nStrategy for Selective Catalytic Hydrogenation Independent of Remote\nChain Length","volume":"141","author":"Bender","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"2026073021262282200_cit16","doi-asserted-by":"publisher","first-page":"15838","DOI":"10.1021\/jacs.5c03926","article-title":"One-Pot \u201cClick\u201d Synthesis\nof Ring-in-Rings Complexes\nwith Customizable \u03c0-Stacked Dyads","volume":"147","author":"Liu","year":"2025","journal-title":"J.\nAm. Chem. 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Sci."},{"key":"2026073021262282200_cit31","doi-asserted-by":"publisher","first-page":"9928","DOI":"10.1002\/anie.201914513","article-title":"Visible-Light-Excited\nRoom-Temperature Phosphorescence in Water by Cucurbit[8]uril-Mediated\nSupramolecular Assembly","volume":"59","author":"Wang","year":"2020","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026073021262282200_cit32","doi-asserted-by":"publisher","first-page":"506","DOI":"10.1039\/B810669J","article-title":"Reversible\nElectronic Energy Transfer: A Means to Govern Excited-State Properties\nof Supramolecular Systems","volume":"39","author":"Lavie-Cambot","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"2026073021262282200_cit33","doi-asserted-by":"publisher","first-page":"23433","DOI":"10.1039\/D0CP03981K","article-title":"Supramolecular and Suprabiomolecular\nPhotochemistry: A Perspective Overview","volume":"22","author":"Dutta Choudhury","year":"2020","journal-title":"Phys.\nChem. Chem. Phys."},{"key":"2026073021262282200_cit34","volume-title":"Principles of Molecular\nPhotochemistry: An Introduction","author":"Turro","year":"2009"},{"key":"2026073021262282200_cit35","doi-asserted-by":"publisher","first-page":"617","DOI":"10.1146\/annurev-physchem-061020-053433","article-title":"Understanding\nand Controlling Intersystem Crossing in Molecules","volume":"72","author":"Marian","year":"2021","journal-title":"Annu. Rev. Phys. Chem."},{"key":"2026073021262282200_cit36","doi-asserted-by":"publisher","first-page":"187","DOI":"10.1002\/wcms.83","article-title":"Spin\u2212Orbit\nCoupling and Intersystem Crossing in Molecules","volume":"2","author":"Marian","year":"2012","journal-title":"WIREs Comput. Mol. Sci."},{"key":"2026073021262282200_cit37","doi-asserted-by":"publisher","first-page":"107886","DOI":"10.1016\/j.dyepig.2019.107886","article-title":"Enhanced Intersystem\nCrossing to Achieve Long-Lived Excitons Based\non Inhibited Molecular Motion and Rigid Structure","volume":"173","author":"Kong","year":"2020","journal-title":"Dyes Pigm."},{"key":"2026073021262282200_cit38","doi-asserted-by":"publisher","first-page":"732","DOI":"10.1021\/jacs.2c12605","article-title":"Triplets\nwith a Twist: Ultrafast Intersystem Crossing in a Series of Electron\nAcceptor Materials Driven by Conformational Disorder","volume":"145","author":"Murali","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"2026073021262282200_cit39","doi-asserted-by":"publisher","first-page":"6975","DOI":"10.1021\/acs.chemrev.7b00617","article-title":"Spin-Vibronic Mechanism\nfor Intersystem Crossing","volume":"118","author":"Penfold","year":"2018","journal-title":"Chem. 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Ed."},{"key":"2026073021262282200_cit54","doi-asserted-by":"publisher","first-page":"2044","DOI":"10.31635\/ccschem.025.202405229","article-title":"A Supramolecular Catalyst\nfor Selective Photo-Oxidation with Catalytic Amount Enabled by Activating\nSubstrates into Radicals","volume":"7","author":"Tang","year":"2025","journal-title":"CCS Chem."},{"key":"2026073021262282200_cit55","doi-asserted-by":"publisher","first-page":"7403","DOI":"10.1002\/anie.201916732","article-title":"Supramolecular Photocatalysis by\nUtilizing the Host\u2212Guest\nCharge-Transfer Interaction: Visible-Light-Induced Generation of Triplet\nAnthracenes for [4 + 2] Cycloaddition Reactions","volume":"59","author":"Uchikura","year":"2020","journal-title":"Angew. Chem., Int. 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Photobiol."},{"key":"2026073021262282200_cit62","doi-asserted-by":"publisher","first-page":"26556","DOI":"10.1021\/jacs.4c10757","article-title":"Light-Induced\nAntiferromagnetic to\nFerromagnetic Transition in Halogen Substituted 1,4-Bis(imidazolyl)benzene\nSystems: An Effect of Spin\u2212Orbit Coupling and \u03c0-Stacking\nin Enhanced Photomagnetism","volume":"146","author":"Saha","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026073021262282200_cit63","doi-asserted-by":"publisher","first-page":"8357","DOI":"10.1039\/C7SC04125J","article-title":"Supramolecular\nCatalyst\nFunctions in Catalytic Amount: Cucurbit[8]uril Accelerates the Photodimerization\nof Brooker\u2019s Merocyanine","volume":"8","author":"Kang","year":"2017","journal-title":"Chem. 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